Shi et al. have performed an epoxidation of a 2,2-di-substituted alkenylsilane using a catalyst derived from a sugar to obtain an epoxysilane with a selectivity of 94% ee, however, there is such a drawback that an equivalent catalyst is necessary (Non-patent Documents 1 to 4). From the introduction of a silyl group having a large steric hindrance into a vinyl-position, it is expected that the enantio-face selectivity is further enhanced, however, there is a problem that the large steric hindrance hinders the reaction (Non-patent Documents 5 and 6).
[Non-patent Document 1]
Wong, O. A.; Shi, Y. Chem. Rev. 2008, 108, 3958.
[Non-patent Document 2]
Shi, Y. Acc. Chem. Res. 2004, 37, 488.
[Non-patent Document 3]
Yang, D. Acc. Chem. Res. 2004, 37, 497.
[Non-patent Document 4]
Warren, J. D.; Shi, Y. J. Org. Chem. 1999, 64, 7675.
[Non-patent Document 5]
Kobayashi, Y.; Ito, T.; Yamakawa, I.; Urabe, H.; Sato, F. Synlett 1991, 811.
[Non-patent Document 6]
Katsuki, T. Tetrahedron. Lett. 1984, 25, 2821.